


Babysitter For a Day

by DerWille



Series: Little Losers' Club [1]
Category: IT (2017), IT - Stephen King
Genre: ABDL, Age Play, Bathing/Washing, CG/L, Diapers, Embarrassment, Fluff, Infantilism, Light-Hearted, M/M, Non-Sexual Age Play, Omorashi, Wetting, spoon feeding, training pants
Language: English
Status: In-Progress
Published: 2018-11-18
Updated: 2018-12-29
Packaged: 2019-08-25 07:35:59
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 6,215
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16656928
Author URL: https://archiveofourown.org/users/DerWille/pseuds/DerWille
Summary: Although Bill and Stan were both satisfied with the way things were going, Bill had always been interested in expanding their play to include some of their friends. Stan was open to the idea, but reluctant. He felt intensely vulnerable in his role, and even though he was excited to experience that in the safety of Bill’s presence, he wasn’t so sure what it would be like with some of their other friends. Bill was planning on getting him a “babysitter” this afternoon for a few hours while he went off to class. Stan had considered Eddie. Eddie would be good. He was clinical, meticulous, and took these kinds of things seriously.What Stan had not considered was the playful Richie Tozier.





	1. Baby's Day In

**Author's Note:**

> I fixed a lot of the weird tense problems. This was originally just a dialogue, so a lot of the narration was in the present tense. Hopefully it's easier to read now. It's definitely easier to write.
> 
> Chapter 1 is Stan/Richie with Bill.  
> Chapter 2 is Stan/Eddie with Bill.

Nothing seemed amiss in the sleepy residential neighborhood where Bill and Stan lived. Nestled in foliage older than the young men, the shabby house served as a comfortable reprieve from the stresses of the local university, which both they and their friends have attended for the past few years. Neither Stan nor Bill recalled exactly how they added a sort of caregiving dynamic, but over the years it had developed handsomely into a well established ageplay relationship. Stan was deeply satisfied with the structure, order, and predictability of Bill’s caregiving, and Bill was calmed by having someone to take care of and watch out for like a little brother. Engaging in this arrangement from time to time did wonders to soothe both of them from the burdens and obligations of young adulthood.

Although Bill and Stan were both satisfied with the way things were going, Bill had always been interested in expanding their play to include some of their friends. Stan was open to the idea, but reluctant. He felt intensely vulnerable in his role, and even though he was excited to experience that in the safety of Bill’s presence, he wasn’t so sure what it would be like with some of their other friends. Bill was planning on getting him a “babysitter” this afternoon for a few hours while he went off to class. Stan had considered Eddie. Eddie would be good. He was clinical, meticulous, and took these kinds of things seriously.

What Stan had not considered was the playful Richie Tozier. Unfortunately, he currently found himself in his normal street clothes (except for his well hidden training pants), sitting in his kitchen, being spoon fed by his most rambunctious best friend.

“Such a messy eater, Stanny-boy! Must not be feeling this apple sauce. ‘Comin’ in quite low, good chap, requesting permission to land!’ Aw, c’mon, open up for the airplane! You’re killing me, Stanley. Now look, it’s all over your shirt! Didn’t Bill leave a bib?” Richie asked a scoffing Stan.

“I don’t need a bib. I’m not a baby,” Stan said.

“That’s right, you’re a big boy, aren’t you Staniel? Who’s a big boy? Huh? Yes, you are! Now, how ‘bout ya show me just how big you are and get most of this apple sauce in your mouth instead of your face!” Richie crooned sweetly.

Stan hesitated for a moment. Didn’t Richie know how to make it the way Stan liked? Stan spoke up, saying, “Sometimes, Bill puts cinnamon in it. I like it that way.”

Richie grinned. “Yeah? Insider knowledge, huh? Well, let’s see what ol’ Chez Rich can cook up.”

Richie began to dig through the kitchen cabinets looking for cinnamon. Upon finding some, he also grabbed a dish towel. Turning back to Stan, he said, “Here we go. All right, just a pinch of this and that and...BAM! Sauce a la mode!”

Stan rolled his eyes. “That’s not what that means.”

“Language is alive, kiddo. Here, let’s tie this towel around your neck so we don’t mess up your pretty little outfit anymore than we already have.” And with that, Richie started wiping Stan’s face. 

“I can do it myself, Richie!” Stan protested.

“I bet you can, you’re such a big boy! A little cranky, though, don’t you think? Is it almost naptime? Jeez.”

“I yearn for a Richie-free naptime.” Stan muttered.

“I love you too, bud.” Richie replied with a saccharine smile.

Spoon feeding someone is a surprisingly intimate experience. You can feel all of the tiny muscle movements of their mouth and tongue through the spoon in your hand. Both participants engage in a coordinated dance, sweeping and swooning, trying to line up spoon to mouth. Some couples are more graceful than others, however.

“Richie! You’re doing that on purpose!” 

Richie mock-gasped, “You wound me, Stanny! What’s the point of the bib if we don’t use it? Here, allow me to help.”

“I can do it myself, I-” Stan was cut off as Richie moved to tenderly wipe his face with the bib.

“There we go! All ship-shape and ready for more sailing! Can you say ‘arrggh’ bucko? ‘Open up ye mouth and let the pirate ship into the secret cove!’ Good boy! You’re quite a prodigy at eating, way beyond your peers!”

Stan grew tired with the tedium of this feeding. Richie was a lot more aggressive than Bill ever has been! Not to mention, Stan began to notice the inklings of an urge in his bladder.

“Are we almost done with this? I kind of have to -” 

“Two more bites, good sir!” Richie responded cheerfully.

“Fine. Do you, uh, do you know when Bill is coming back?” Stan asked.

“One bite left, Stanny-boy! Make it all gone for your obscenely attractive baby-sitter! Bill will be back in a few hours. Don’t worry your pretty little head about it. Richie will cater to your every need.”

Stan groaned.

“I think I want Bill to come back now.”

“Sorry, tiger. You’re stuck with ol’ Rich for the time being.” Richie replied.

Stan’s eyes fell to the floor, searching for the least embarrassing way to communicate his growing need to use the bathroom. He squirmed in the seat, shifting his weight from side to side. His right hand began to slowly stroke his left wrist in a small, repetitive circle.

“You got kind of quiet there, champ. Not too thrilled with the programming for the near future?” Richie probed.

“I, um… usually Bill let’s me -”

Richie cut him off once more.“I know exactly what you’re looking for! Bill told me all about your after-meal ritual. I’ll be right back lickety-split!” 

Stan sat confused, quietly more desperate as the seconds tick by. Bill frequently asked him if he needs to use the bathroom. He knew how embarrassed Stan gets about such things, and it made Stan feel so little and safe and cared for to have that burden lifted from him. It was something decided early on that that would be a dynamic in their play. The slight humiliation of being dependent on someone else for something so basic as a filling bladder always jettisoned Stan into a meek and vulnerable headspace. Unfortunately for Stan, Richie didn’t seem to be aware of his own role to play. Maybe Bill didn’t mention this part to him? His thoughts were rudely interrupted by Richie saying, “Here we go, bucko! Don’t think your good pal Richie would forget your afternoon bottle.”

“It’s not a bottle, Richie. I’m not -”

“A baby, yeah, yeah, old news, Stanny-Boy. A sippy-cup, whatever, call it what you want. Uncle Richie wants you to drink this whole thing before you get out of that chair. So you grow up to be a big strong boy like Bill and I! Then, we can go play or nap or do whatever you like, alright good chap?”  
Stan tried once more to alert Richie to his dilemma, saying, “I, um. I need to...uh”

“Not so fast, mister! I made it just like how Bill said! Chocolate milk, but not too much chocolate. You’re not gonna weasel your way out of this. I want you to drink the whole thing down right now. Unless you want me to hold it for you?”

Growing more frustrated with the situation, Stan responded, “No! I’m not a baby, Richie. I can do it myself.”

“That’s my big boy!” Richie praised.

Richie handed Stan the sippy cup. It was an opaque plastic thing with a twist on lid and open spout to suck on; a glorified bottle, but a bottle with dignity (as Stan liked to think). Without being sure of how much longer he could hold on without wetting himself, Stan raised the sippy cup to his lips and cautiously suckles. It’s pretty good; Richie did a decent job. Stan bursts out in a deep blush as he realizes that Richie was smugly watching him drink from the sippy cup.

“Good, isn’t it? I told ya, at Chez Rich it’s only the best for my best bud!”

Stan reluctantly nodded. He sipped and swallowed methodically. The growing pressure in his lower belly called out to him, the presence of even more liquid doing nothing to increase his confidence in his ability to resist imminently flooding his pants. And. Then. 

A small whine escaped Stan’s throat as he finishes the sippy cup. Losing control, a small spurt burst into his training pants. Richie, busy cleaning up from the feeding, wasn’t paying attention at all as Stan’s small trickle quickly devolved into a deluge. The liquid scorched his thighs and groin as it sloshed around before being slowly absorbed by his faithful training pants. Simultaneously, Stan’s face bloomed into a volcanic shade of humiliation as he erupted into a series of choked sobs. He jumped up from his seat as Richie turned around to see what all the commotion is about.

“Woah, woah, woah, Stan, what’s wrong?” 

Stan helplessly shifted back and forth between his feet as his accident began to leak out into his shorts. Richie’s eyes grew huge with realization as Stan brought his hands between his legs and felt the wetness. Stan’s gaze dropped to the floor.

“Oh bud, what happened? Bill said you could take care of business yourself.”

Stan’s frustration boiled over, and he exploded at Richie. “It’s your fault! It’s all your fault! I didn’t want to do this but Bill said you could handle it but you never asked me if I had to go and you didn’t make the apple sauce the right way and now I’m all gross and I...I can’t stand being dirty like this!”

Stan collapsed his head into his hands, sobbing. Everything was wrong. This was not the way things were supposed to go. This was not following the plan. He already felt so silly sharing this thing of his and Bill’s with Richie, and now here he was pissing his pants in front of one of his best friends. Like a weirdo. Having a tantrum. Like a baby.

Richie glided up behind Stanley and placed a hand on his shoulder. At first, Stan shrugged away, but relented when Richie tried again. Richie made quiet, consoling sounds as he rubbed a small circle into Stan’s upper back.

“Hey. Hey, big guy. It’s ok. You didn’t do anything wrong. It’s cool if you’re mad at me. I, um, didn’t know you had to...go potty.”

“I didn’t have to “go potty.”” Stan said indignantly.

Richie smirked. “Well, you definitely don’t have to anymore, huh bud?”

“Richie. Don’t.” Stan whispered, hackles raised.

Richie turned serious for a moment. “Sorry. I’m sorry, Stanley, ok? I was supposed to take care of you and I messed up. I didn’t think to check with you. I figured you were so independent with the feeding, you know, so adventurous and confident and headstrong, that I didn’t even consider I’d need to think about...um...this. Well, actually, considering how lunch went maybe I should’ve been on the lookout…”

“Richie!” Stan exclaimed.

“Sorry! Alright. We got this. Let’s just. Ok. How about we go get your diaper changed, kiddo?”

Stan’s head flipped around to face Richie. “It is NOT a diaper. I am not a baby.”

“Well, maybe if it were this wouldn’t have happened.” Richie said quietly.

Stan grew quiet at that comment, failing to come up with a suitable retort. It was true. If he were wearing a diaper then he could have...wet…himself and it probably would have been fine until BIll came back. 

“This has actually never happened before…” Stan mumbled.

Richie gasped with exaggerated excitement. “Oooh! Baby’s first diaper change, just for little ol’ me here? Don’t worry, Stanny-Boy, Uncle Richie is on the job! I’ll get you whipped up into some fresh Pampers before you know it! No soggy bottoms on my watch, no siree! I’ll have you wiped down, powdered, and taped up before you can say-”

Stan grimaced throughout Richie’s tirade and put his foot down, “Richie! This is not a diaper, I am not a baby, and you will not be involved with this at all! Just...just go get me some new pants. And socks. And underwear. Maybe a towel. I’m going to go shower.” 

“You mean you want some new pull ups?” Richie asked.

“No. This part of the afternoon is over. Do not tell anyone about this. Ever.” Stan was adamant.

“Aw darn. And here I was thinking I was gonna get to see my best friend through his potty training woes! I’m a reliable comforter, Staniel! I can be consolation in your great time of need!”

Stan walked off into the bathroom without acknowledging Richie. Richie sighed, wiping a faux-tear from his eye. “They grow up so fast…”

 

**************************

Later that afternoon, Bill returned to find Stan and Richie sitting in the living room watching Netflix. Richie greeted him as he walks in saying, “Billiam, my good lad! I had such a wonderful time with your little pal here. He’s definitely a cutie patootie, I’ll tell ya that.”

“W-w-well thanks, Richie. Did it g-go well, Stan?”

“As well as could be expected, I guess.” Stan responded with reservation.

Richie hooted, saying, “The highest of praise from such a grumpy pumpkin! He was a treat, Big Bill. I’ll watch the little tyke anytime! Got to run now. I’m a popular fellow, you see.”

Richie walked to the door, before pausing. He looked back at Stan. “Oh, and Stan? Keep trying, sport. You’ll get the hand of keeping your pants dry soon!”

And with that, Richie left. Stan muffled a gasp of surprise and did his best to avoid eye contact with Bill, who had a confused smirk on his face.

“What w-was that about?” Bill asked.

“It’s nothing. It’s just Richie. You know how it is.”

Bill was not convinced. “Hm. Is my b-big boy not so big?”

“This conversation is over.” Stan firmly replied.

Bill laughed heartily before mentioning that maybe Richie will have to babysit more often.


	2. Babysitter For a Night

“Love y-you too, bud.” “Bath t-time is at 7:30, and he’ll probably try to get a second bottle of chocolate milk, but y-you shouldn’t indulge that.” Bill furrowed his brow as he tried to remember the rest of the guidelines to the feeding and care of Stanley Uris. “Oh! You’ll need to check that he’s wearing his special pr-protection before bed. It’s something w-w-we’ve been doing recently.”

“What does that involve exactly?” Eddie asked, as though he were studying for a stressful final exam.

“His d-dia-diaper. He’ll be pretty embarrassed about it. He may need help, it kinda j-just depends on how little he feels at th-the time. You should also take him to the bathroom throughout the day. I guess I f-f-forgot to mention that to Richie, and it didn’t go very w-well…”

“Wait a minute! You had Richie do this before me? Richie can barely remember to tie his own shoes! He’s the one in need of a babysitter.” Eddie exclaimed.

“I won’t stop you. Who k-knows what he’s into?” Bill joked. Eddie blushed a bit, pondering the idea. Maybe it was something to consider for later?

“I wouldn’t be surprised. Don’t worry, Bill. I’m sure I can handle Stanley for a night. Just drive safe and I’ll call you if anything comes up.” Eddie began to take off his backpack. Bill gave one last glance around the room making sure that he hasn’t forgotten anything.

“I’ll arrive at the hotel in a few hours and then the c-c-conference is tomorrow morning. Stan is probably in the living room. He’s already had dinner, but m-may want a snack soon. Make s-s-sure he uses his words.” Eddie watched as Bill sort of hemmed and hawed in the doorway. Eddie rolled his eyes, but could not help thinking that it sure was cute to see Bill anxious about leaving Stan in this way. He placed a hand on Bill’s shoulder, saying, “Really, Big Bill. It’ll be fine. I’m taking this very seriously and Stan will be very safe and cared for.”

Bill smiled gratefully. “Thanks, Eddie. I’m j-just gonna say goodbye to Stan.”

They both walked into the living room and found Stan sitting on the couch on his phone. He looked up as Bill and Eddie approached.

“Are you leaving now?” Stan asked in a small voice.

“Y-yeah, big guy. I’ll be back tomorrow afternoon. I w-w-want you to be a good boy for Eddie when I’m gone.”

Stan’s mouth curled into a slight smile. “I’m always a good boy.”  
Bill gave a knowing grin, and said, “You know that’s not always t-true.” He pulled Stan into a hug. “I’ll miss you.”

“I’ll miss you too. Do a good job with your presentation. I know you can do it.” Stan held on tighter to the larger man.

“Thanks, bud.” Bill slowly withdrew from the hug. He set his shoulders in resignation. “I’ll see you g-guys tomorrow.” With a last look at Stan and Eddie, he collected his backpack and headed out of the house.  
*********************************************************************************************

 

At first, Eddie didn’t know what exactly to do with Stan. He wasn’t a child, and yet he wasn’t exactly behaving like the friend he had known for so long. Eddie had always known Stan as a highly responsible and effortlessly competent person, one who longed for the perception and attainment of maturity. And now Eddie was supposed to make sure he went to the bathroom and got to bed on time? It was perplexing to say the least.

Eddie silently watched Stan in the living room for a few moments after Bill’s departure. Feeling the growing tension in the air, and not wanting to make the situation any more awkward than it already was, Eddie spoke up. “Hey, Stanley.”

“Hello,” Stan replied hesitantly.

Pleased with the interaction thus far, Eddie tried again.

“What are you up to?”

Stan slowly brought his eyes up from the floor to meet Eddie’s. “I’m just playing with my phone, I guess.”

Eddie nodded, “That sounds fun. Are you excited for tonight? I mean, like, do you feel OK with me doing all of this?”

Stan seemed to mull it over in his head a bit before responding. “I think it’ll be ok. I’m scared, but I also think it could be fun. There’s no way it could be worse than with Richie.”

“No offense, but Richie seems kind of like a strange choice for something like this, ya know? I’m a little hurt that I wasn’t the first choice. Not really, but maybe a little bit. What exactly was so bad about it anyway?” Eddie asked.

Stan grimaced almost imperceptibly before replying, “I don’t really want to talk about it.” He turned back to look at his phone, leaving Eddie to feel slightly guilty for bringing the topic up.

“That’s ok! I mean, there are so many things I have planned that we can do! I promise that I’ll be a much more attentive caretaker than that Trashmouth.”

Glancing up from his phone, Stan timidly nodded before returning to his screen.

“Now then. First things first! Do you need to go to the bathroom?”

A light blush appeared across Stan’s cheeks. “Um...I’m good, thanks.”

“Oh, did you already go? Should I check? You’ve been kind of quiet over there. Are you still dry, Stanley?” Eddie asked.

Seeming to almost grow smaller, Stan scoffed petulantly. “Eddie! I didn’t have an accident and I don’t need to go to the bathroom.”

And then Eddie uttered the words that would determine the dynamic for the rest of the night:

“Why don’t you just try for me, just to be sure?”

Stan regressed even more upon hearing the request before silently getting up from the couch and walking into the bathroom.

“And make sure to wash your hands!” Eddie called after him. Oh yeah, he thought to himself. I know exactly how to deal with this now. 

*************************************************************************************************************

To say that Eddie was bossy would be an understatement. After Stan returned from the bathroom and had his hands checked, Eddie told Stan that they were going to color with some crayons that Eddie brought. Eddie then had Stan color with only his non-dominant hand for “authenticity.” It was a good exercise in feeling small, however. Especially when Eddie had Stan present his finished products to be hung on the fridge for when Bill came back. 

 

Bath time proved a bit more of a challenge. Eddie’s desire for cleanliness clashed with Stan’s desire for privacy. The compromise involved plenty of bubbles in the bath to cover Stan’s nudity and Eddie had to turn around while Stan undressed. It didn’t help that Eddie absolutely had to wash Stan’s hair himself, as he knew the most effective way to keep hair clean, apparently. What Eddie wasn’t so sure of was how to address getting Stan dressed for bed.

“It’s time to get out of the bath, Stan. I don’t want you to prune. Let’s get you ready for bed.” Eddie stood patiently in the bathroom as Stanley arranged his bath toys along the edge of the tub.

“I’m not tired,” Stanley reflexively replied, almost as if following a script.

“I think you are tired. I hope you’re not going to get grumpy with me, big guy. Do you know how important it is for children to get enough sleep? It changes the way their brains develop! That’s like, huge, Stan!”

Stan considered this for a moment before replying, “My brain is mostly developed by now. I’m sure it can manage for another hour.”

Eddie scoffed. “Stanley Uris, you are going to get out of the tub right now and we are going to get you ready for bed!”

Stan cowered at Eddie’s shrill command, before asking in a quiet voice, “Can you hand me my towel and turn around?”

Eddie rolled his eyes at Stan’s modesty while holding the towel out to him. “Really Stanley, it’s nothing I haven’t seen before.”

Stan waited for Eddie to turn around before standing up from the bath and wrapping the towel around his waist. “Ok, you can look now.”

Eddie smiled softly. Stan’s modesty was endearing. It would be a problem, however, when it came to getting him dressed for bed. Eddie was determined to see this through, and confidently broached the subject, saying, “Let’s get you dressed, champ.”

Stan calmly replied, “I can get dressed by myself. I don’t need your help.”

Eddie was prepared for some resistance. “Bill told me that you need help getting your special underwear on.”

Stan’s face drained of color at the mention of his “special underwear.” He stammered a bit before saying, “That’s just something I wear for Bill. I don’t actually need it, and I especially don’t need your help with it.”

Eddie was not convinced. He led Stanley to his bedroom, saying, “I think we’d both feel better if you were protected during the night. It’s not a big deal, Stan. Let me help you get your diaper on.”

Stan stammered at the mention of the ‘d’ word. “It’s not a diaper,” he began to say, as Eddie held up the crinkly, printed object in his hand. It was obviously a diaper. Sized just right for Stanley, but looking like a toddler’s diaper with happy cartoon prints and tapes. Stan kept quiet.

Eddie noticed Stan’s reluctance, and felt for his embarrassed friend. “Look, Stanley. How about I unfold it and lay it out and then I’ll turn around and you can lay down and pull it up. Then I can tape it up and make sure it’s on right and I don’t have to see your uh...unmentionables.”

Stan blushed at the fact that they were actually talking about how best to put a diaper on him, but Eddie’s plan seemed ok. He nodded hesitantly.

Eddie beamed. “Ok, good! Here, I’ll lay it out on the bed and then you can lay down on it.” Eddie struggled with what side to put where, but eventually Stan rolled his eyes and came over to help. A bit flustered, Eddie said, “Hey! I’ve never done this before. I haven’t been in diapers in like twenty years! And that’s more than can be said of some people.”

Stan blushed at the comment before motioning for Eddie to turn away. As Eddie turned around, Stan slowly dropped his towel before settling himself down on the unfolded diaper. He rustled around a bit, trying to find the right fit. Bill usually did this part. Satisfied with his positioning, Stan pulled the diaper up between his legs.

Eddie turned around at this moment and approached Stan to help with the tapes. Stan shot out a “I can do it myself” before looking away from Eddie’s skeptical face. “Do you know how hard it is to get urine out of fabric, Stanley? You’d have to watch the sheets like four times! Just let me do it and it’ll fit much better.” 

Finicking with the tapes was a minor challenge, but Eddie succeeded after having Stan put his arms behind his head and out of the way. Eddie announced Stan completely diapered, and began helping him into his two piece pajama outfit. Stan began feeling quite tired, even though it was only 8:30. Eddie, remembering Stan’s protestations about not being tired earlier in the evening, felt vindicated. He also thought Stan was adorable. After getting Stan completely dressed, he pulled Stan up into a long hug. Stan melted into Eddie, enjoying the embrace. His eyes shot wide open, however, as he felt Eddie pull the back of his pajama pants and diaper away and begin to shake some baby powder down his backside.

“Eddie! What are you doing?!”

“Chill out, Stanley, it’s corn starch based. Not that talc stuff that gives you cancer. It’s important to me that you don’t chafe in the middle of the night. Besides, you’ll smell good for Bill in the morning. Or, at least better.”

Stanley rolled his eyes before climbing back into bed and covering himself with his comforter. Eddie stroked his hair for a moment and whispered a quiet “good night.” Stan mumbled something in return before turning over and quickly falling asleep. 

Eddie slowly closed Stan’s door, leaving it open just a crack. He sighed in relief and felt pretty accomplished at wrangling Stan Uris into bed.

**********************************************************************************************************

The next afternoon, Eddie met Bill as as he returned home.

“H-how was he?” Bill asked.

“He was good. He’s taking a little nap in the living room.” Eddie reported.

“Did h-h-he put up a fight at bedtime?”

“I was able to deal with him. He’s still in his diaper, though. He was dry this morning and I figured why waste one. He didn’t seem to mind. Too much, at least.” Eddie bragged. 

Bill smiled. “That’s r-really cute. I wasn’t s-sure if he’d let you see him i-in it or not. He’s pretty shy about that.”

“Pretty shy about what?” Stan appeared behind Eddie, excited to see Bill.

“H-hey buddy! I missed you!” Bill enveloped Stan into a big hug. Stan rested his head on Bill’s shoulder and sighed.

“You’re s-s-so cute with your padded rear, buddy.” Bill joked. Stan groaned as Bill let out a belly laugh.

Eddie smiled at the exchange. “Well, I better be going. Richie will probably be going crazy now without me. I have so many ideas to uh..try. Anyhow. It was fun, Stan! Next time I won’t be so easy on you.” With a wink and a grin, Eddie walked out.

Bill and Stan looked at each other for a moment. “You don’t think he meant that he and Richie were going to...try this, right? Stan asked.

“I don’t know b-bud. It works for us, d-d-doesn’t it?”

“I guess,” Stan responded.

“Anyway, i-is my little boy still d-dry?” 

“Bill, I swear to God. You know I only wear them for you.” 

“Love y-you too, bud.”


	3. Trying Something New

The ice rink wasn’t very busy that afternoon. It was just Stan, Bill, and a few strangers slowly skating in long circles across the ice. Bill was a much more elegant skater than Stan, who preferred more structured physical activities than just mindlessly slipping and sliding around a forty year old failing ice rink. However, this was what Bill wanted to do today and so Stanley was happy to accompany him.

Carefully inching forward on his trembling legs, Stan moved methodically around the ice, with Bill quite literally skating circles around him. Stan had on his blue mittens to protect his hands from the cold and also from when he catches himself falling on the ice. At the begging of Bill, he was also protected in another way. It was hard to tell, but the keen eye would notice a slight bulge around Stan’s waist. Not that any stranger here would be on the lookout, or even notice it at all. Stan mostly wore a diaper today because it brought so much joy to Bill. It was a secret they shared between them, a symbol of their unique bond that only they were aware of. In the public eye they were able to discreetly engage in their special relationship.

Stan fell to the ground for the third time in the fifteen minutes since they started skating. Bill effortlessly glided over to him.

“Are y-you ok?” He asked.

Stan rolled his eyes and let out a whiny sigh. “I don’t know why you like this so much. It’s cold and I can barely move.”

“Yeah, b-but it doesn’t hurt as much when you fall on your butt, does it?” Bill replied suggestively.

Stan gave him a steely glare and responds, “You know I only do this to make you happy.”

Bill’s face lit up. “I am v-very grateful. Now come on, m-m-mister grumpy pants! I have to t-teach you how to go fast!” Bill skated enthusiastically around Stan, before falling gracelessly on his own behind.

Stan lets out a chuckle. “Maybe you’re the one that needs the padding,” he taunted.

Stan felt pretty silly shuffling around the ice. Something about not being able to move very well humbled him, putting him into a more vulnerable headspace. He was relying on Bill to move around and basically teach him how to skate. The whole scene reminded Stan of a parent teaching their young child how to walk; combined with the soft diaper hidden under his jeans, Stan felt very small.

Bill’s playful barbs and teasing left Stan red-faced. After picking himself once again from the cold ice, Stan suggested that they stop for a moment and take a break.

“Do you want some h-hot chocolate?” Bill asked as they slowly made their way to the edge of the rink. He pointed out the small concession stand in the distance.

“W-we could just take a break and warm up a little.”

“Yeah. Ok,” Stan replied in a small voice.

Bill took notice of this smaller-voiced Stan. Bill knew that Stan seemed more fragile when he was feeling little. Bill was trying more to steer Stan towards feeling that he could turn his vulnerability while feeling small into a greater intimacy with others, instead of culminating in embarrassment and self-rejection.

“Y-y-you’re doing a really g-good job today. Thank you for humoring m-me. It’s fun when I g-get to teach you how to do s-something for a change.” Bill complimented.

Stan grew red at the praise, before wrapping his arms around Bill and saying, “Anytime. Thank you for being patient.”

Both young men reached the exit to the rink and hobbled over to a bench where they could remove their ice skates. Bill unlaced his quite easily, while Stan struggled with untangling his. Once Bill had removed his skates and put his shoes back on, he glanced over at Stan, who had just only got his first skate off.

“Do y-you want me to help you?” Bill asked softly. 

Stan nodded and slowly stopped fidgeting with his laces before leaning back and looking expectantly at Bill.

Bill took the lead and pulled Stan’s skated-foot into his lap, making quick work of the tightly wound laces.

“Thanks. I don’t know why I couldn’t do it myself.”  
“You’re j-just too little, I guess. It’s ok to l-let people help you sometimes.” Bill said.

Stan smiled and rolled his eyes as he pulled his foot out of Bill’s lap to drag his shoes on.

“Let’s go get some hot chocolate and warm up for a bit.”

*******************************************************************************************************

After a bit of teasing from Bill as to whether Stan could hold his own cup without help, or whether they should’ve brought a bib, both friends finished their hot chocolate and stood up to leave the ice rink.

Stan stretched his arms up and above his head, feeling the length in his shoulders and back before hurriedly dropping them again as he felt his undershirt ride up, potentially revealing his “special underwear.” As he thought about that close call, he realized that he should go to the bathroom. Of course, he’d have to ask Bill first.

“Um, Bill? I kind of need to go to the bathroom. So I’m going to go do that, ok?”

Bill smiled mischievously. “Th-that’s not how this works, and y-y-you know it, Stanley! You agreed that I w-would need to give you permission first. To h-help you feel small.”

“Oh, of course, we’re doing this whole thing to help me, right? It definitely has nothing to do with you and your “interests.” You’re a completely unbiased bystander.” Stan huffed.

Bill smiled to himself, before replying, “I think you should t-try the d-d-diaper.”

Stan hissed, “Not so loud! Other people will hear! And I don’t want to do that with all these people around. We’re too far away from home and I like to get clean pretty soon after.”

“Aw, c-come on, Stan! Just b-be a good b-boy for me? It won’t feel wet, you’ll just feel warmer. I promise it’s n-not that bad! It c-c-can actually be pr-pretty fun.” Bill argued.

“And how exactly would you know that, Bill Denbrough? I thought you were just into one side of this.” Stan accused.

“Th-there are many things I k-keep to myself, Stanley. W-will you just try? I promise it w-will be ok.”

Stan sighed. “The things I do for you, Big Bill. So, like. What do I do? Just, you know… go?”

Bill’s eyes smiled. “That’s the idea, sp-sport. Just try and relax.”

They both stood there not saying anything for a few moments. Stan felt uncomfortable.

“I don’t know if I can go on command with you watching me.”

“Th-that’s alright. Let’s go w-walk around a bit.”

They took off from the concession stand and meandered out of the ice rink, chatting about this and that. Midway through Bill’s explanation of his Christmas break plans, Stan was able to let loose a small trickle. He gasped as it quickly turned into a flood. Warmth cascaded into his diaper, sloshing around his groin and in between his thighs before being absorbed and wicked away from Stan’s skin. 

Bill gave Stan a strange look before he realized why his friend had stopped walking and had turned redder than a fire hydrant. He let out a small chuckle.

“Are you g-going now?” He asked playfully.

Stan did not respond. He stood stock still as he emptied his bladder into his pants. For a moment, Stan was terrified of leaking and making his private accident very much a public one, but the diaper was much more absorbent and dependable than the flimsy training pants he sometimes wore. Absolutely know one, other than Bill and Stan, knew what was happening. And then it was over.

Stan didn’t dare to move as the last of the liquid settled into his diaper. He tentatively examined the flood of feelings that he was experiencing. The diaper didn’t feel wet, necessarily. It was just sort of warm, like Bill had said. It had also expanded quite a bit. He could feel it push apart his legs as it rubbed up against his inner thighs. As Stan came out of his introspection, he realized that Bill was beaming at him.

“Ugh. Are you happy now?” He said to Bill.

“Y-yup. How is it?” Bill replied.

Stan shifted his weight from foot to foot before responding, “It’s very warm. It’s not as bad as I thought, or as bad as the training pants feel when wet. I think I want out of it now, though.”

Bill laughed. “W-well let’s get back home, then.” They both turned to walk towards their car in the parking lot, when Bill noticed that Stan had a slight waddle to account for the expanded diaper. He couldn’t help teasing a little.

“Y-you must be a heavy wetter, sport. You’re waddling l-like a toddler who desperately needs a ch-change.” 

Stan blushed, looked at the ground, before he said with a small smile, “Bill, I swear to God, the things I do for you…” 

Bill laughed as Stan’s smile suddenly disappeared when he felt the squish on his bottom as he sat down in Bill’s passenger seat.

“Let’s go g-get you some fresh pants, b-big boy.”

Stan thought he had never heard such a good idea.


End file.
